This invention relates to novel benzylsulfonylureas. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, e.g., herbicides.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA0 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA0 R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA0 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA0 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom; PA0 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA0 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA0 W and Q are independently oxygen or sulfur; PA0 n is 0, 1 or 2; PA0 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA0 Y is methyl or methoxy; or their agriculturally suitable salts; provided that: PA0 L is SO.sub.2 NR.sub.6 R.sub.7, OCH.sub.3, OC.sub.2 H.sub.5, CO.sub.2 CH.sub.3 or CO.sub.2 C.sub.2 H.sub.5 ; PA0 R.sub.2 is H, Cl, Br, F, CF.sub.3 or OCH.sub.3 ; PA0 R.sub.4 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 Cl, or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA0 R.sub.5 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA0 R.sub.6 and R.sub.7 are independently C.sub.1 -C.sub.3 alkyl; PA0 R.sub.8 is H or CH.sub.3 ; PA0 R.sub.9 is H or C.sub.1 -C.sub.3 alkyl; PA0 R.sub.3 is ##STR11## W is O or S; X is CH.sub.3, OCH.sub.3 or Cl; PA0 Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA0 Z is CH or N; PA0 X.sub.1 is H, Cl, CH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA0 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA0 X.sub.3 is CH.sub.3 or OCH.sub.3 ; and PA0 Y.sub.1 is CH.sub.3 or OCH.sub.3 ; PA0 (1) when W is S, then R.sub.8 is H; PA0 (2) the total number of carbon atoms of R.sub.6 and R.sub.7 is less than or equal to 4; and PA0 (3) when X is Cl, then Z is CH and Y is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or OCH.sub.3. PA0 (1) Compounds of Formula I wherein PA0 (2) Compounds of Preferred (1) wherein PA0 (3) Compounds of Preferred (2) wherein PA0 (4) Compounds of Preferred (3) wherein R.sub.3 is ##STR12## (5) Compounds of Preferred (4) wherein R.sub.1 CF.sub.3, NO.sub.2, CO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 N(OCH.sub.3)CH.sub.3 or OSO.sub.2 CH.sub.3 ; and PA0 (6) Compounds of Preferred (5) wherein X and Y are independently CH.sub.3 or OCH.sub.3. PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)methanesulf onamide, m.p. 207.degree.-208.degree.; PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)methan esulfonamide, m.p. 185.degree.-188.degree.; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)methan esulfonamide, m.p. 194.degree.-195.degree.; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)m ethanesulfonamide, m.p. 165.degree.-168.degree.; PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)methanesulfo namide, m.p. 192.degree.-194.degree.; PA0 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester, m.p. 179.degree.-183.degree.; PA0 2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonylmethyl]ben zoic acid, methyl ester, m.p. 154.degree.-156.degree.; PA0 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]ben zoic acid, methyl ester, m.p. 162.degree.-165.degree.; PA0 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonylmethy l]benzoic acid, methyl ester, m.p. 135.degree.-140.degree.; PA0 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester, m.p. 165.degree.-167.degree.; PA0 2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonylmethyl]benz oic acid, methyl ester, m.p. 125.degree.-130.degree.; and PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-(2-methylsulfonyloxyphenyl )methanesulfonamide, m.p. 202.degree.-204.degree.(d). PA0 L is SO.sub.2 NR.sub.6 R.sub.7, OCH.sub.3, OC.sub.2 H.sub.5, CO.sub.2 CH.sub.3 or CO.sub.2 C.sub.2 H.sub.5 ; PA0 R.sub.2 is H, Cl, Br, F, CF.sub.3 or OCH.sub.3 ; PA0 R.sub.4 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 Cl, or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA0 R.sub.5 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA0 R.sub.6 and R.sub.7 are independently C.sub.1 -C.sub.3 alkyl; and PA0 R.sub.9 is H or C.sub.1 -C.sub.3 alkyl; PA0 (1) Compounds of Formula II wherein R.sub.2 is H; PA0 (2) Compounds of Preferred (1) wherein R.sub.1 is CF.sub.3, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, CO.sub.2 R.sub.4, SO.sub.2 R.sub.5, SO.sub.2 NR.sub.6 R.sub.7, SO.sub.2 N(OCH.sub.3)CH.sub.3 or OSO.sub.2 R.sub.5 ; and PA0 (3) Compounds of Preferred (2) wherein PA0 R.sub.1, R.sub.2 and R.sub.9 are as previously defined. PA0 Braker, Sheehan, Spitzmiller and Lott, J. Am. Chem. Soc., 69, 3072 (1947); PA0 Mitter and Bhattacharya, Quart. J. Indian. Chem. Soc., 4, 152 (1927); PA0 Shrage and Hitchings, J. Org. Chem., 16, 1153 (1951); PA0 E. Bisayni et al., Bull. Soc. Chem. Fr., 803 (1969); PA0 Caldwell, Kornfeld and Donnell, J. Am. Chem. Soc., 63, 2188 (1941); and PA0 Fissekis, Myles and Brown, J. Org. Chem., 29, 2670 (1964).
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R.sub.1 is hydrogen or lower saturated aliphatic acyl; and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl or ##STR5## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6## Based upon similarity to a known compound, the author speculated that the foregoing compound might have a hypoglycemic activity.
Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sco., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR7## wherein R=H or CH.sub.3.
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula: ##STR8## wherein R.sub.1 is ##STR9## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA1 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA1 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA1 R.sub.2 is H; PA1 R.sub.8 is H; and PA1 W is O; PA1 R.sub.1 is CF.sub.3, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, CO.sub.2 R.sub.4, SO.sub.2 R.sub.5, SO.sub.2 NR.sub.6 R.sub.7, SO.sub.2 N(OCH.sub.3)CH.sub.3 or OSO.sub.2 R.sub.5 ; PA1 R.sub.9 is H; PA1 X.sub.3 is OCH.sub.3 ; and PA1 Y.sub.1 is OCH.sub.3 ; PA1 R.sub.4 is CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sub.5 is CH.sub.3 or CF.sub.3 ; and PA1 R.sub.6 and R.sub.7 are independently CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sub.4 is CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sub.5 is CH.sub.3 or CF.sub.3 ; and PA1 R.sub.6 and R.sub.7 are independently CH.sub.3 or C.sub.2 H.sub.5.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.